3. Moby and Natalie Portman

Yes, Natalie Portman went out with Moby back in 2001. It makes no sense to us either.

The musician told Spin that he was on the receiving end of a bit of abuse following the romance.

I guess in some people’s eyes, [nerds] might be mildly sexy — and, as a nerd, I’m certainly happy to enjoy some of the effects of that — but as far as the very brief affair I had with Natalie, it’s made me the target of a lot of nerd wrath. You can’t date Luke Skywalker’s mom and not have them hate your guts.

7. Courteney Cox and Michael Keaton

Cox and Keaton went out for five years before breaking up in 1995. At the time, Cox called the relationship “the most important relationship I’ve ever had” and said Keaton was “the most wonderful person I’ve ever met”.

Aw </3

8. Justin Timberlake and Fergie

Source: PA Archive/Press Association Images

Fergie dated JT when he was 16 years old and she was 23 years old. Needless to say, it didn’t last very long. As she told Cosmopolitan:

Justin and I would go out together and have fun and make out. We went to Hawaii together, but we were never serious. He was Mr. Right Now.

9. Andre Agassi and Barbra Streisand

Source: AP/Press Association Images

Agassi dated Streisand while he was at the peak of his tennis powers. Agassi wrote about the relationship in his autobiography:

We agree that we’re good for each other, and so what if she’s twenty-eight years older? We’re simpatico, and the public outcry only adds spice to our connection. It makes our friendship feel forbidden, taboo – another piece of my overall rebellion. Dating Barbra Streisand is like wearing Hot Lava.

It didn’t last.

10. Ashley Olsen and Lance Armstrong

Back in 2007, Armstrong and Olsen were spotted on several dates. According to Juliet Macur’s biography of the athlete, the head of Livestrong Foundation advised Armstrong that dating Olsen could harm his image and urged him to end the relationship.

Armstrong was reportedly reluctant to end the relationship…

She’s twenty-one … F**k you.

…but it soon fizzled out anyway.

¯\_(ツ)_/¯

11. Alanis Morrissette and Ryan Reynolds

Source: PA Archive/Press Association Images

You, you, you oughta know that these two were engaged.

12. Whoopi Goldberg and Ted Danson

Source: AP/Press Association Images

Danson and Goldberg were a thing back in the 90s after they met on the set of Made in America. By all accounts, they were absolutely mad for each other, with Danson once remarking:

I’d walk in Whoopi’s shadow for the rest of my life—I adore the woman.